There is no box around the keel pivot on my boat. I do get water in but it is via the hole in the cockpit. It is just a bit enough to be annoying. I don't have the wooden piece around the pivot either. You may have some cracks in that box. If you can raise the boat on the trailer. Drop the keel and inspect the inside of the housing. I sailed mine in 20 knots water almost coming in over the side. But no water inside. Oh, be sure never to drob the keel in the water the housing is not designed to withstand that impact. I will replace my worm driven winch with a strap winch like to put in on the trailer. Change the strap for synthetic rope. No hard cables. Good luck
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